This past weekend, a group of friends and I enjoyed a marvelous staycation at the historic Chicago Athletic Association.  We, Jennifer, Jessica, Adrienne and I, were there to celebrate our beautiful friend, Sarah’s birthday with her.  I have to say, it was by far one of the best hotel experiences I’ve had in a long time.  I checked in first, as the room was under my name, and as soon I walked in I was lost.

The building is full of nooks and crannies and staircases leading to somewhere you’re not quite sure you’re supposed to be.  I had to ask where the check in desk was, because it was not immediately apparent to me, at the information desk on the first floor, which also housed a Shake Shack, a gift shop through a labyrinth of hallways and a long, long line up to the famed Cindy’s Rooftop (more on that later).

Upon check-in, I received five tokens (one for each of us) for champagne in one of the six restaurants/bars at the Chicago Athletic Association, the Cherry Circle Room.  After I got lost once again trying to find the elevators up to the guest rooms, I dropped off my bags in our double-bedded room and went back downstairs to get take some photos of the beautiful property.

Lo and behold, I was lost again and ran smack dab into one of my roommates for the evening, Adrienne.  Gleefully, we made our way back up to the room together to set up for an evening of champagne and relaxation in our Wes Anderson meets your hip rich uncle’s spare bedroom room.  We had snacks and booze and spa supplies and cards, all of which make for a perfect evening.

However, we did not get to much of what we planned in the room, as the Athletic Association had other plans for us.  Once everyone had arrived, we left the room to get our free champagne and plan our evening in the Cherry Circle Room, which is adjacent to the Game Room, a bar with bocce ball and foosball and shuffleboard, on the second floor.

The Cherry Circle Room was fully committed for the evening which was fair, seeing how it was a beautiful, wood-paneled dream of a restaurant.  They accommodated us in the small lounge just outside it’s doors, where they served us champagne in pretty flutes.  We sipped and schemed; all of us agreed that we needed to see their ballroom before we did anything else.

After finishing the gratis bubbly, we took the elevator to the eighth floor and barged in on the set up of the evening’s event.  As the staff graciously guided us back towards the elevator, we snuck peaks of the beautiful White City Ballroom.  The gentleman who was ushering us good-naturedly back to approved areas overheard us talking about going up to Cindy’s and stopped what he was doing to personally escort us up via the back elevator, effectively saving us a good thirty minutes waiting in line on the ground floor.

That was the start of our good luck.  Once in the bar, we ran into one of my old friends from work and the rest is a haze of champagne and charcuterie.  We took the requisite photos on the terrace and marveled over the view from the top.  We sipped champagne and cocktails and got a light dinner to share.  It was amazing, and it was said more than once how unbelievable the service and libations were.

After having more than our fair share of expertly mixed cocktails, we made our way back to the room to continue the evening.  After face masks (by Crude), nail polish, more champagne, Mike and Dave Need Wedding Dates, and drunk snacks, we all fell asleep in our cozy hotel robes.

The next morning, we awoke early to headaches and the need to see the sunrise from the ballroom we only got a small glimpse of the night before.  The trip was a secret mission through the employee entrance but it was successful.  The pink sky from the east facing windows was too pretty for words; it shined over the glass front buildings and the bean, with the turquoise lake in the background.

The ballroom was just stunning; a perfect mix of modern touches and classic architecture.  We also peeped into the Madison Ballroom, which featured city views and grand chandeliers.  When we got back to the room, we fell back asleep for a morning nap, then took turns enjoying the luxurious shower.

After pampering just a little bit more, we worked our way down to the Milk Room for a satisfying breakfast of toast, bacon, and the best hash brown cakes I’ve ever had.  They were crispy on the outside and creamy with sliced green onions on the inside.  The Milk Room was located in the hotel lobby, and was a warm collection of wood, mismatched chairs and colorful pillows.

The food, along with the restaurant’s amazing coffee, brought us back to life enough to pack up he room and check out.   I think we all needed this weekend, it was perfectly restorative and fun and we enjoyed every minute of it.

Have you stayed at the Chicago Athletic Association? Which restaurant was your favorite?